1: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 2: 93 percent / 48percent HBr / ethanol / 1 h 3: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: HCl gas / methanol / 1) 0 deg C, 1 h, 2) 0 deg C to rt, 1.5 h<br />2: K₂CO₃ / acetone / 12 h / Heating<br />3: 49 percent / Et₃N, Ph₃P / Pd(OAc)2 / 17 h / 80 &deg;C<br />4: 95 percent / H₂ / Pd/C / ethanol / 4 h<br />5: 86 percent / (COCl)2 / CH₂Cl₂; dimethylsulfoxide / 1 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 95 percent / H₂ / Pd/C / ethanol / 4 h<br />2: 86 percent / (COCl)2 / CH₂Cl₂; dimethylsulfoxide / 1 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 49 percent / Et₃N, Ph₃P / Pd(OAc)2 / 17 h / 80 &deg;C<br />2: 95 percent / H₂ / Pd/C / ethanol / 4 h<br />3: 86 percent / (COCl)2 / CH₂Cl₂; dimethylsulfoxide / 1 h / -78 &deg;C<br /> <br /> &nbsp;